As discussed here: Offering actual money as a bounty? offering actual money as a bounty sets the wrong incentives. However I would suggest giving users the ability to pay with money for offering a bounty regardless of their reputation. The bounty would still count as reputation for the receiving user but would not be discounted from the paying user's reputation.

@ShadowWizard the bounty will not come from the reputation from any user. It's would be just reputation that gets awarded to the accepted answer.
– jcfreiMar 28 '18 at 13:28

3

@ShadowWizard I don't know if this is due to all the time I spent translating the encrypted SharePoint documentation into human-readable text.... but it seems pretty clear: The original proposal suggested to add money bounties to the system - User A post a bounty, the awarded user gets the money. Here he is suggesting the ability to buy a bounty instead: you pay to post the bounty but the awarded user gets rep points in proportion to what you paid.
– ΝеvеrꭑoꭇеMar 28 '18 at 13:29

@Derpy thanks, close vote retracted, downvote stays. I think this is horrible idea which will harm SE a great deal.
– Shadow WizardMar 28 '18 at 13:31

1

I'd have let you contract with me to add bounties for you, but it looks like they're cracking down on online human trafficking, so no deal :(
– Won'tMar 28 '18 at 14:21

On the front, everyone is happy. You basically introduced micro-transactions in StackExchange business model, which would seem a good idea to finally help the network solving its financial issues...

BUT

Let's see what you have actually done: you have just implemented an official, approved way for anyone to buy rep for another user. Yep, that's right - bounties are awarded by the person who posts them (unless he forgets to).
So, under your assumption, someone can pay to give "free" reputation to any user he choices".

This is bad. Very bad. RegEx based HTML parsing level of bad.
Given enough time, this would go out of hand - now users can just "Pay-To-Win" to:

get more rep points by using socks or voting rings to self-award bounties and thus more "visibility", by which I mean that inexperienced users are naturally inclined to trust more users with a lot of rep.... After all, isn't rep just "a rough measure of how much the community trusts you"?

pay to unlock moderator level special powers on the site

perform shady practices like "bounty selling" far more easily since the bounty rep has to come from nowhere

even assuming good trust with no sock involved, "bounty gambling" (post a bounty on a post you own, hope the attracted upvotes exceed the bounty cost) suddenly becomes even more easy to do

will undersell developer work even more, by offering a sort of "cheap outsourcing / do my homework" alternative to hiring and paying a developer what he really deserves. Thanks to PeterJ for pointing out this very important point I missed. If you need some work done fast, pay someone who put his life in that experience field what he deserves.

and so on...

Also consider that getting actual money in the picture would inevitably make handling system abuse far more problematic. Just think of a sockpupet / voting ring that also involves paid-with-real-money rep.... the Staff would have an hard time facing all the legal threats users will make when the bounty they paid for gets reversed because of a voting irregularity.

Sorry, this would only lend itself to problems... The system isn't just laid out to handle "paid help-desk services" and any attempt to steer it in that direction will probably just end up in a big mess.

However I would suggest giving users the ability to pay for offering a bounty regardless of their reputation.

No, that would only result in a lot of (non-closable) bounty questions issued by low rep users, who just want to encourage answers for their low quality questions, just because they're able to spend money for them.

I believe that's a very bad idea.

The bounty would still count as reputation for the receiving user.

Reputation given away for bounties needs to originate from somewhere/someone.
Any user doing so should be aware of that consequence, and be encouraged to have good reasons to give their own reputation points away for it.

Dealing with actual money, is completely out of question here. The site is based on users volunteering, and monetarization (beyond SE's own business) is totally out of scope, and never will be implemented.